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144 Holiday homes

(1) Very Good 

30

Province of Siena / Castellina In Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £120 / night

£474 - £715 / week

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from £120 / night

20

Province of Siena / Castellina In Chianti

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

 …see more

from £108 / night

£755 / week

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from £108 / night

100

Castellina - small - Castellina In Chianti apartment sleeps 2

Province of Siena / Castellina In Chianti

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
These apartments are ideal for a romantic escape in Tuscany. Both apartments comes with fire burning fireplace, a small but refined living room with sofa bed an equipped kitchenette and a double king size bedroom and bathroom with shower. Both apartments have windows op  …see more

from £99 / night

£688 - £972 / week

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from £99 / night

14

Province of Siena / Castellina In Chianti

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly

 …see more

from £42 / night

£275 - £487 / week

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from £42 / night

(2) Excellent 

48

Province of Siena / Castellina In Chianti

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 150 km
  • Child friendly
  • Private garden

 …see more

from £104 / night

£475 - £561 / week

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from £104 / night

13

Il Granaio - Castellina In Chianti house sleeps 6

Province of Siena / Castellina In Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Luxury interior designed 2 bedroom house in stunning position in Chianti countryside with a private garden (half acre) and 2 terccaces. Shared swimming pool and tennis courts within a medieval village setting. 12km from Castellina in Chianti, 7km from Poggibonsi. Stunn  …see more

from £83 / night

£575 - £750 / week

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from £83 / night

(2) Very Good 

100

Castellina In Chianti 81687 - Castellina In Chianti villa sleeps 10

Province of Siena / Castellina In Chianti

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa dating back to the first 800 as is present in the Catasto Leopoldino (the first inventory in Tuscany), it has been restructured maintaining it Tuscan typical style with ceilings with beams in wood and floors in cooked and window "mandorlate" that the  …see more

from £338 / night

£1976 - £2961 / week

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from £338 / night

(3) Excellent 

24

Siena Chianti Farmhouse Flat - Castellina In Chianti apartment sleeps 8

Province of Siena / Castellina In Chianti

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 90 km
  • Child friendly
  • Private garden
Immersed in the country but within walking distance of Castellina in Chianti, a 150 sq.m. apartment in an old stone, Chianti farmhouse with its own big, enclosed private garden. The rooms are all large, the ceilings are beamed and terracotta tiled, floors terracotta til  …see more

from £100 / night

£694 - £755 / week

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from £100 / night

16

Villa Fontana - Castellina In Chianti villa sleeps 8

Province of Siena / Castellina In Chianti

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
This beautiful, detached stone farmhouse, situated near Castellina in Chianti, was restored in 1995. Surrounded by ample private grounds, it sits in a panoramic position and is reached by its own driveway.The garden spaces and external paved terraces are all abundantly  …see more

from £545 / night

£2177 - £3888 / week

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from £545 / night

14

Le Stalle, Podere Patrignone - Castellina In Chianti apartment sleeps 5

Province of Siena / Castellina In Chianti

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Rather unglamorously, this apartment used to house livestock owned by the tenant farmers. However, the transformation could not be more complete. Two large beautiful arched windows are the main feature of this bright 2-bedroom apartment.A covered entrance leads to a ver  …see more

from £186 / night

£1113 - £1436 / week

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from £186 / night

(2) Excellent 

17

Province of Siena / Castellina In Chianti

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Ask about pets

 …see more

from £37 / night

£259 / week

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from £37 / night

24

Villa Rosa - Castellina In Chianti villa sleeps 12

Province of Siena / Castellina In Chianti

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Everything about this property is classically Tuscan. If you dream of typical Tuscany as breathtaking panoramas, misty hills covered in precision lines of vineyards, olive groves, gravel roads and driveways shadily lined with pointy cypress trees, and grand villas with  …see more

from £573 / night

£4009 / week

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from £573 / night

8

Il Torrino - Castellina In Chianti villa sleeps 7

Province of Siena / Castellina In Chianti

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
Inside, the property is set over 3 floors. On the ground floor, there is an open plan living and dining area, a separate well equipped kitchen, bathroom and 2 double bedrooms. A spiral staircase leads guests up the watchtower to a pretty single bedroom. Another spiral s  …see more

from £181 / night

£1261 - £2348 / week

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from £181 / night

100

Castellina In Chianti 48549 - Castellina In Chianti villa sleeps 8

Province of Siena / Castellina In Chianti

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful stone farmhouse with private pool situated in quiet and panoramic location. This villa is nestling deep amidst the Chianti Classico hills and woods and is the ideal place to spend a relaxing holiday in close contact with nature. A large 8000 square-meter garde  …see more

from £416 / night

£2910 - £4232 / week

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from £416 / night

13

La Tinaia - beautiful 1 bedroom cottage & garden - Castellina In Chianti cottage sleeps 2

Province of Siena / Castellina In Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Private garden
Podere Patrignone is a beautiful old 15th Century estate ('podere') which has been lovingly and tastefully restored. Patrignone is set on top of it's own hill reached by a long, winding private road that ends at Patrignone. It is set in 150 acres of fores  …see more

from £130 / night

£776 - £957 / week

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from £130 / night

100

Castellina - large - Castellina In Chianti apartment sleeps 6

Province of Siena / Castellina In Chianti

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
All the large apartments are located in Dario's House that is the oldest building of the Hamlet. This beautiful stone building that imposes its structure on the Valley was an old watch little fortified house. The building has been carefully restored and divided into apa  …see more

from £160 / night

£1117 - £1485 / week

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from £160 / night

(3) Very Good 

24

Province of Siena / Castellina In Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly

 …see more

from £198 / night

£1382 / week

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from £198 / night

100

Castellina In Chianti 46441 - Castellina In Chianti villa sleeps 16

Province of Siena / Castellina In Chianti

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful restored farmhouse with swimming-pool situated in the heart of the Chianti Classico area, a few kilometers away from Castellina in Chianti. This property is quietly situated on a large 220-hectare farming estate producing excellent wines. Tastefully furnished,  …see more

from £392 / night

£2739 - £2747 / week

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from £392 / night

100

Castellina - Torre - Castellina In Chianti apartment sleeps 6

Province of Siena / Castellina In Chianti

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
Torre is an old stone tower converted in a independent small villa. The accommodation has two nice double bedrooms and two bathrooms, a little studio, kitchen, sitting room, and a big living room with double sofa bed and working fireplace.This small villa in Tuscany is  …see more

from £186 / night

£1298 - £1672 / week

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from £186 / night

(2) Excellent 

20

Casa del Fico - Castellina In Chianti farmhouse sleeps 6

Province of Siena / Castellina In Chianti

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
The house forms part of the oldest wing of Le Bagnaie, a 300 year old farm on a secluded hilltop, which was converted into 8 privately owned houses in 1990. All are beautifully restored in traditional rustic style, with exposed beams, old terracotta floors and open fir  …see more

from £165 / night

£1150 - £1450 / week

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from £165 / night

100

Castellina - middle - Castellina In Chianti apartment sleeps 5

Province of Siena / Castellina In Chianti

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
Some of the middle  size apartments are located in the old school for children of the hamlet while some others are located in the old house of the estate ranger and in the oldest building of the farm called Darios House. All middle size apartment two double bedroom  …see more

from £105 / night

£731 - £1044 / week

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from £105 / night

(1) Excellent 

24

Villa Patrignone 7 bedroom Tuscany villa with pool - Castellina In Chianti villa sleeps 14

Province of Siena / Castellina In Chianti

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
Villa Patrignone has 7 large double bedrooms, each with private bathroom, a cavernous kitchen-dining room with large fireplace, and a lovely living room, with high vaulted ceilings, comfortable sofas and a library. The house was built sometime in the 1500s and still has  …see more

from £394 / night

£2358 - £4072 / week

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from £394 / night

16

Luxury Chianti apartment with shared pool, private garden, barbecue - Castellina In Chianti castle sleeps 4

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Come to the heart of the Chianti region to discover a wonderfully charming inn and agritourism facility that offers hotel-like amenities in elegant apartment suites, set in the evocative atmosphere of the Tuscan hills. Resting on a rolling hill, the Borgo is located  …see more

from £137 / night

£954 - £1322 / week

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from £137 / night

(1) Very Good 

24

Apartment 510 - Castellina In Chianti apartment sleeps 6

Province of Siena / Castellina In Chianti

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
Bed places: 6 +1Four rooms, 90 sqm, fully equipped kitchen and living room, 3 double bedrooms (one with high window). Inside, each bedroom has TV and bathroom with shower (total 3 baths). On the ground floor with a private terrace with tables, chairs and umbrellas. It i  …see more

from £143 / night

£996 / week

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from £143 / night

16

Province of Siena / Castellina In Chianti

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £199 / night

£1207 / week

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from £199 / night

25

Province of Siena / Castellina In Chianti

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £105 / night

£696 - £957 / week

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from £105 / night

30

Province of Siena / Castellina In Chianti

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min

 …see more

from £78 / night

£432 / week

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from £78 / night

14

LOFT AGRITURISMO IL CELLESE - Castellina In Chianti farmhouse sleeps 4

Province of Siena / Castellina In Chianti

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Located between Florence and Siena, its undulating hills evoke the refined country life of antiquity while maintaining its beauty and balance. Along its extensive terrain, oak forests alternate with cypress, vineyards and centennial olive trees. Here, the best Tuscan w  …see more

Pricing unknown

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Pricing unknown

18

FORNO AGRITURISMO IL CELLESE - Castellina In Chianti farmhouse sleeps 3

Province of Siena / Castellina In Chianti

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Located between Florence and Siena, its undulating hills evoke the refined country life of antiquity while maintaining its beauty and balance. Along its extensive terrain, oak forests alternate with cypress, vineyards and centennial olive trees. Here, the best Tuscan w  …see more

Pricing unknown

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Pricing unknown

16

Province of Siena / Castellina In Chianti

9 16 Min stay varies

  • 9 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

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Pricing unknown

15

Apartment 507 - Castellina In Chianti apartment sleeps 2

Province of Siena / Castellina In Chianti

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
Bed places : 2Two Rooms, 40 sqm, a kitchen and tv, a double bedroom, a bathroom with shower. The apartments are at the first floor. On the ground floor externally there are tables, chairs and umbrellas for common use. Can host one more child (max 12 years) with accommod  …see more

from £61 / night

£423 / week

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from £61 / night

23

FIENILE AGRITURISMO IL CELLESE - Castellina In Chianti farmhouse sleeps 5

Province of Siena / Castellina In Chianti

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Located between Florence and Siena, its undulating hills evoke the refined country life of antiquity while maintaining its beauty and balance. Along its extensive terrain, oak forests alternate with cypress, vineyards and centennial olive trees. Here, the best Tuscan w  …see more

Pricing unknown

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Pricing unknown

100

Ester - Castellina In Chianti villa sleeps 12

Province of Siena / Castellina In Chianti

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly
ExteriorsLocated in the heart of the Chianti region, this extraordinary villa boasts views over the hills, the valleys and the countryside at its fullest. It is situated very close to Castellina in Chianti, a town in the province of Siena with ancient constructions, an  …see more

from £347 / night

£2426 / week

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from £347 / night

14

NICCHIE AGRITURISMO IL CELLESE - Castellina In Chianti farmhouse sleeps 7

Province of Siena / Castellina In Chianti

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Located between Florence and Siena, its undulating hills evoke the refined country life of antiquity while maintaining its beauty and balance. Along its extensive terrain, oak forests alternate with cypress, vineyards and centennial olive trees. Here, the best Tuscan w  …see more

Pricing unknown

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Pricing unknown

13

CISPIANO AGRITURISM IL CELLESE - Castellina In Chianti farmhouse sleeps 6

Province of Siena / Castellina In Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Located between Florence and Siena, its undulating hills evoke the refined country life of antiquity while maintaining its beauty and balance. Along its extensive terrain, oak forests alternate with cypress, vineyards and centennial olive trees. Here, the best Tuscan w  …see more

from £130 / night

£518 - £1035 / week

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from £130 / night

10

15462-Apartment Chianti - Castellina In Chianti apartment sleeps 5

Province of Siena / Castellina In Chianti

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Three Bedroom Ground Floor Apartment Chianti Castellina is a charming apartment, part of a farmhouse situated in beautiful Chianti countryside. The apartment opens onto its own lovely shaded terrace with table and chairs for dining al fresco, and there is more space fo  …see more

from £50 / night

£344 - £384 / week

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from £50 / night

24

SUITE " SERGIO " - Castellina In Chianti farmhouse sleeps 6

Province of Siena / Castellina In Chianti

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
Sergio is a two storey ground floor apartment at the one end of the main building. It has a private furnished terrace that overlooks the olive groves, vineyards ande the picturesque countryside.Entry is directly into the main living room, complete with a wood burning fi  …see more

from £173 / night

£1035 - £1509 / week

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from £173 / night

30

APARTMENT RENTAL: 2 BEDROOMS, SLEEPS 7 IN CASTELLI - Castellina In Chianti apartment sleeps 7

Province of Siena / Castellina In Chianti

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden
In the prestigious area of Chianti, the most visited in Tuscany, you will find this charmimg 80 m2 appartment in a lovely hamlet with all the conforts you need in order to truly enjoy your holidays and relax in our swimming pool and tennis court with stunning views. Th  …see more

from £83 / night

£580 / week

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from £83 / night

24

Province of Siena / Castellina In Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 85 km
  • Child friendly
  • Private garden

 …see more

from £69 / night

£483 / week

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from £69 / night

100

Castellina In Chianti 44148 - Castellina In Chianti villa sleeps 6

Province of Siena / Castellina In Chianti

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beautiful independent villa with swimming-pool situated near Castellina in Chianti, in the heart of the Chianti Classico area. This property was recovered by restoring the outbuilding of an ancient manor house. The restoration was very accurate and aimed to preserve the  …see more

from £160 / night

£1120 - £1125 / week

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from £160 / night

Top Destination reviews

Farm holidays in Chianti
A Christams dream

This year my husband and I decided to spend Christmas on our own, in the Chianti countryside. La Capanna delle Cozzole is just the perfect location: very quiet, romantic and private location. In the village you can find top quality food, wine and d … see more

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